Title: Five Cays Adventure Vacations 2026 | Expedia.com

![](https://images.trvl-media.com/place/11672/d2d90a11-08a9-4e50-887d-b91554f7945e.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Five Cays Adventure Vacations

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## Top Adventure vacation packages in Five Cays

Price found within the past 48 hours. Click for updated prices.

![Windsong on the Reef](https://images.trvl-media.com/lodging/3000000/2430000/2422200/2422198/76aaffd4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Windsong on the Reef

Grace Bay

Save 100% on your flight

$2,030

per person

Jun 15 - Jun 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9.2/10 Wonderful! (1,026 reviews)

Wingsong was fabulous! They were extremely accommodating when we needed to move our dates last minute. The front desk and Butler staff is 10/10\. The resort is not too big which is nice bc never seems too busy even when they are fully booked. There are several dining options and the food is good. The beach is beautiful and the people are so nice. I would recommend getting a car bc taxi's around the island, to town and to restaurants are very expensive.

Reviewed on Apr 2, 2026

![Beachfront at Windsong on the Reef](https://images.trvl-media.com/lodging/21000000/20850000/20846500/20846403/159db57d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Beachfront at Windsong on the Reef

Grace Bay

Save 100% on your flight

$2,808

per person

Jun 15 - Jun 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9.2/10 Wonderful! (122 reviews)

I was worried about our stay having read previous travelers reviews - but my whole family loved our stay at windsong. The property was in great shape, clean and tidy. Lots of towels on the loungers well before we were up. Plenty of room for everyone to get a great seat on the beach or by the pools. The staff were very friendly and kind - shout out to Travis! The food was fine, breakfast was great and worth the money and we did several lunches and one dinner. Expect all food to be expensive no matter where you eat, you’re on a tiny island that needs to import everything. We will definitely stay here again!

Reviewed on Mar 17, 2026

![Bungalows at Windsong on the Reef](https://images.trvl-media.com/lodging/2000000/1800000/1793300/1793291/bb54e1cd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Bungalows at Windsong on the Reef

Grace Bay

Save 100% on your flight

$2,349

per person

Jun 15 - Jun 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9/10 Wonderful! (86 reviews)

The upgraded us into a room in the main hotel which is unbelievable. Very laid-back but beautiful

Reviewed on Mar 9, 2026

![The Shore Club Turks and Caicos](https://images.trvl-media.com/lodging/16000000/15440000/15438900/15438835/fb1fd0ea_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Shore Club Turks and Caicos

Long Bay

Save 100% on your flight

$3,138

per person

Jun 15 - Jun 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9.4/10 Exceptional! (907 reviews)

Awesome resort! Restaurants were great too. Rooms were clean with nice views. Pools and amenities were exceptional. The beach was wonderful, lots of activities if you choose. Entire staff was helpful, Khem, Sley, Love, Fortune, David... too many to mention, all great. Excellent location for relaxation and peace and quiet. Atmosphere was relaxing and comfortable. Good value.

Reviewed on Mar 17, 2026

![Ambergris Cay Private Island - All-Inclusive](https://images.trvl-media.com/lodging/31000000/30970000/30962100/30962027/65016aeb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Ambergris Cay Private Island - All-Inclusive

Save 100% on your flight

$6,076

per person

Jun 7 - Jun 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9.6/10 Exceptional! (22 reviews)

We had a very nice stay. Will definitely come back

Reviewed on Mar 20, 2026

Don't see what you're looking for?

See all available trips from Columbus to Five Cays

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-03/2026-05-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MDS&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Adventure vacations in Five Cays

Price found within the past 48 hours. Click for updated prices.

![Beachfront at Windsong on the Reef](https://images.trvl-media.com/lodging/21000000/20850000/20846500/20846403/159db57d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Beachfront at Windsong on the Reef

Grace Bay

Save 100% on your flight

$2,808

per person

Jun 15 - Jun 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9.2/10 Wonderful! (122 reviews)

I was worried about our stay having read previous travelers reviews - but my whole family loved our stay at windsong. The property was in great shape, clean and tidy. Lots of towels on the loungers well before we were up. Plenty of room for everyone to get a great seat on the beach or by the pools. The staff were very friendly and kind - shout out to Travis! The food was fine, breakfast was great and worth the money and we did several lunches and one dinner. Expect all food to be expensive no matter where you eat, you’re on a tiny island that needs to import everything. We will definitely stay here again!

Reviewed on Mar 17, 2026

![The Shore Club Turks and Caicos](https://images.trvl-media.com/lodging/16000000/15440000/15438900/15438835/fb1fd0ea_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Shore Club Turks and Caicos

Long Bay

Save 100% on your flight

$3,138

per person

Jun 15 - Jun 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9.4/10 Exceptional! (907 reviews)

Awesome resort! Restaurants were great too. Rooms were clean with nice views. Pools and amenities were exceptional. The beach was wonderful, lots of activities if you choose. Entire staff was helpful, Khem, Sley, Love, Fortune, David... too many to mention, all great. Excellent location for relaxation and peace and quiet. Atmosphere was relaxing and comfortable. Good value.

Reviewed on Mar 17, 2026

![Ambergris Cay Private Island - All-Inclusive](https://images.trvl-media.com/lodging/31000000/30970000/30962100/30962027/65016aeb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Ambergris Cay Private Island - All-Inclusive

Save 100% on your flight

$6,076

per person

Jun 7 - Jun 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9.6/10 Exceptional! (22 reviews)

We had a very nice stay. Will definitely come back

Reviewed on Mar 20, 2026

Don't see what you're looking for?

See all available trips from Columbus to Five Cays

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-03/2026-05-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MDS&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Adventure vacations in Five Cays

Price found within the past 48 hours. Click for updated prices.

![Bungalows at Windsong on the Reef](https://images.trvl-media.com/lodging/2000000/1800000/1793300/1793291/bb54e1cd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Bungalows at Windsong on the Reef

Grace Bay

Save 100% on your flight

$1,264

per person

May 8 - May 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9/10 Wonderful! (86 reviews)

The upgraded us into a room in the main hotel which is unbelievable. Very laid-back but beautiful

Reviewed on Mar 9, 2026

![Beachfront at Windsong on the Reef](https://images.trvl-media.com/lodging/21000000/20850000/20846500/20846403/159db57d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Beachfront at Windsong on the Reef

Grace Bay

Save 100% on your flight

$1,422

per person

Jun 5 - Jun 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9.2/10 Wonderful! (122 reviews)

I was worried about our stay having read previous travelers reviews - but my whole family loved our stay at windsong. The property was in great shape, clean and tidy. Lots of towels on the loungers well before we were up. Plenty of room for everyone to get a great seat on the beach or by the pools. The staff were very friendly and kind - shout out to Travis! The food was fine, breakfast was great and worth the money and we did several lunches and one dinner. Expect all food to be expensive no matter where you eat, you’re on a tiny island that needs to import everything. We will definitely stay here again!

Reviewed on Mar 17, 2026

![Rock House](https://images.trvl-media.com/lodging/73000000/72070000/72061500/72061427/779a17b8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Rock House

Blue Mountain

Save 100% on your flight

$2,537

per person

May 8 - May 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9.6/10 Exceptional! (379 reviews)

Property is well situated. Feels private and quiet. Safe as well. Clean. Plenty if things to do. Gym is clean and well maintained.

Reviewed on Mar 26, 2026

Don't see what you're looking for?

See all available trips from Columbus to Five Cays

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-03/2026-05-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MDS&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Adventure vacations in Five Cays

Price found within the past 48 hours. Click for updated prices.

![Windsong on the Reef](https://images.trvl-media.com/lodging/3000000/2430000/2422200/2422198/76aaffd4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Windsong on the Reef

Grace Bay

Save 100% on your flight

$1,554

per person

Jun 19 - Jun 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9.2/10 Wonderful! (1,026 reviews)

Wingsong was fabulous! They were extremely accommodating when we needed to move our dates last minute. The front desk and Butler staff is 10/10\. The resort is not too big which is nice bc never seems too busy even when they are fully booked. There are several dining options and the food is good. The beach is beautiful and the people are so nice. I would recommend getting a car bc taxi's around the island, to town and to restaurants are very expensive.

Reviewed on Apr 2, 2026

![Dream Villas Provo](https://images.trvl-media.com/lodging/97000000/96370000/96368700/96368651/a01ea79e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Dream Villas Provo

Save 100% on your flight

$1,725

per person

May 6 - May 10

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9/10 Wonderful! (58 reviews)

Highly responsive property manager

Reviewed on Apr 1, 2026

![Bungalows at Windsong on the Reef](https://images.trvl-media.com/lodging/2000000/1800000/1793300/1793291/bb54e1cd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Bungalows at Windsong on the Reef

Grace Bay

Save 100% on your flight

$1,771

per person

Jun 19 - Jun 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Providenciales (PLS)

9/10 Wonderful! (86 reviews)

The upgraded us into a room in the main hotel which is unbelievable. Very laid-back but beautiful

Reviewed on Mar 9, 2026

Don't see what you're looking for?

See all available trips from Columbus to Five Cays

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-03/2026-05-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MDS&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Find awesome Five Cays adventure vacations

####  How can I book the best Five Cays adventure trips? 

Choose your own adventure in Five Cays, whether that’s a white-knuckle experience or a weekend walk. Read the reviews of the adventures that have gone before to be sure your chosen stay is your idea of fun. 

####  How can I plan the perfect Five Cays family adventure vacation? 

Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Five Cays. Just make sure to check your chosen escapade is within the realms of can-do for the whole clan and will have the whole team grinning. 

####  Can I book all-inclusive Five Cays adventure vacation packages? 

By refining your filters, you can explore all-amazing, all-adventurous, all-inclusive vacation packages. Amp up the extravagance with a few more filters too. Pick pristine pools, sensational spas, or wondrous waterparks for a sensational adventure getaway. 

####  Why should I book a Five Cays adventure vacation for couples? 

Book a Five Cays couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond. 

####  How can I find the best deals on adventure packages in Five Cays? 

It’s easy to unleash fabulously affordable adventures. Enter the dates for your caper, then sort your search results by price or deals. 

####  Can I book an adventure vacation package in Five Cays with free cancellation and/or flexible dates? 

Yes! When you’re searching for a great getaway, filter by payment option for free cancellation, so a change of plans won’t mess up your adventures. You’ll find buy now, pay later options, too, for full-on flexibility. 

####  Why should I book a Five Cays adventure trip with Expedia? 

Adventure, airfare, accommodation, ATOL protection, and activities—all on one site. And that’s just the benefits that begin with A. 

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## More Vacation Ideas

[Flights to Five Cays

](https://expedia.com/Cheap-Flights-To-Five-Cays.d11672.Travel-Guide-Flights)[

Five Cays Hotels

](https://expedia.com/Five-Cays-Hotels.d11672.Travel-Guide-Hotels)[

Vacation Rentals in Five Cays

](https://expedia.com/Five-Cays-Vacation-Rentals.d11672.Travel-Guide-VacationRentals)[

Car Rentals in Five Cays

](https://expedia.com/Car-Rentals-In-Five-Cays.d11672.Car-Rental-Guide)[

Five Cays Vacations

](https://expedia.com/Five-Cays.d11672.Destination-Travel-Guides)[

Things to do in Five Cays

](https://expedia.com/Things-To-Do-In-Five-Cays.d11672.Travel-Guide-Activities)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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